Record Information
Version 1.0
Update Date 1/22/2018 12:54:53 PM
Metabolite IDPAMDB001641
Identification
Name: Isethionic acid
Description:Isethionic acid (C2H6O4S) is a short chain alkane sulfonate containing hydroxy group, is a water soluble liquid used in the manufacture of mild, biodegradable and high foaming anionic surfactants which provides gentle cleansing and soft skin feel.; A colorless, syrupy, strongly acidic liquid that can form detergents with oleic acid. The Pseudomonas aeruginosa ssuEADCB gene cluster is required for the utilization of alkanesulfonates (such as isethionic acid) as sulfur sources, and is expressed under conditions of sulfate or cysteine starvation.
Structure
Thumb
Synonyms:
  • (2-Hydroxyethyl)sulfonate
  • (2-Hydroxyethyl)sulfonic acid
  • (2-Hydroxyethyl)sulphonate
  • (2-Hydroxyethyl)sulphonic acid
  • 2-Hydroxy-Ethanesulfonate
  • 2-Hydroxy-Ethanesulfonic acid
  • 2-Hydroxy-Ethanesulphonate
  • 2-Hydroxy-Ethanesulphonic acid
  • 2-Hydroxyethane-1-sulfonate
  • 2-Hydroxyethane-1-sulfonic acid
  • 2-Hydroxyethane-1-sulphonate
  • 2-Hydroxyethane-1-sulphonic acid
  • 2-Hydroxyethanesulfonate
  • 2-Hydroxyethanesulfonic acid
  • 2-Hydroxyethanesulphonate
  • 2-Hydroxyethanesulphonic acid
  • 2-Hydroxyethylsulfonate
  • 2-Hydroxyethylsulfonic acid
  • 2-Hydroxyethylsulphonate
  • 2-Hydroxyethylsulphonic acid
  • b-Hydroxyethanesulfonate
  • b-Hydroxyethanesulfonic acid
  • b-Hydroxyethanesulphonate
  • b-Hydroxyethanesulphonic acid
  • Beta-Hydroxyethanesulfonate
  • Beta-Hydroxyethanesulfonic acid
  • Beta-Hydroxyethanesulphonate
  • Beta-Hydroxyethanesulphonic acid
  • Ethanolsulfonate
  • Ethanolsulfonic acid
  • Ethanolsulphonate
  • Ethanolsulphonic acid
  • Hydroxyethylsulfonate
  • Hydroxyethylsulfonic acid
  • Hydroxyethylsulphonate
  • Hydroxyethylsulphonic acid
  • Isethionate
  • Isethionate sodium salt
  • Isethionic acid
  • Isethionic acid sodium salt
  • Kyselina isethionova
  • Potassium 2-hydroxyethanesulfonate
  • Potassium 2-hydroxyethanesulfonic acid
  • Potassium 2-hydroxyethanesulphonate
  • Potassium 2-hydroxyethanesulphonic acid
  • Potassium isethionate
  • Potassium isethionic acid
  • Sodium 2-hydroxyethanesulfonate
  • Sodium 2-hydroxyethanesulfonic acid
  • Sodium 2-hydroxyethanesulphonate
  • Sodium 2-hydroxyethanesulphonic acid
  • Sodium 2-hydroxyethyl sulfonate
  • Sodium 2-hydroxyethyl sulfonic acid
  • Sodium 2-hydroxyethyl sulphonate
  • Sodium 2-hydroxyethyl sulphonic acid
  • Sodium b-hydroxyethanesulfonate
  • Sodium b-hydroxyethanesulfonic acid
  • Sodium b-hydroxyethanesulphonate
  • Sodium b-hydroxyethanesulphonic acid
  • Sodium beta-hydroxyethanesulfonate
  • Sodium beta-hydroxyethanesulfonic acid
  • Sodium beta-hydroxyethanesulphonate
  • Sodium beta-hydroxyethanesulphonic acid
  • Sodium isethionate
  • Sodium isethionic acid
  • Sodium β-hydroxyethanesulfonate
  • Sodium β-hydroxyethanesulfonic acid
  • Sodium β-hydroxyethanesulphonate
  • Sodium β-hydroxyethanesulphonic acid
  • β-Hydroxyethanesulfonate
  • β-Hydroxyethanesulfonic acid
  • β-Hydroxyethanesulphonate
  • β-Hydroxyethanesulphonic acid
Chemical Formula: C2H6O4S
Average Molecular Weight: 126.132
Monoisotopic Molecular Weight: 125.99867937
InChI Key: SUMDYPCJJOFFON-UHFFFAOYSA-N
InChI:InChI=1S/C2H6O4S/c3-1-2-7(4,5)6/h3H,1-2H2,(H,4,5,6)
CAS number: 107-36-8
IUPAC Name:2-hydroxyethane-1-sulfonic acid
Traditional IUPAC Name: sodium isethionate
SMILES:OCCS(O)(=O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as sulfonic acids. These are compounds containing the sulfonic acid group, which has the general structure RS(=O)2OH (R is not a hydrogen atom).
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Sulfonic acids and derivatives
Sub ClassSulfonic acids
Direct Parent Sulfonic acids
Alternative Parents
Substituents
  • Alkanesulfonic acid
  • Sulfonyl
  • Sulfonic acid
  • Hydrocarbon derivative
  • Primary alcohol
  • Organosulfur compound
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-1
Melting point: < 25 °C
Experimental Properties:
PropertyValueSource
Water Solubility:1000 mg/mLPhysProp
Predicted Properties
PropertyValueSource
Water Solubility103.0 mg/mLALOGPS
logP-2.2ALOGPS
logP-2.9ChemAxon
logS-0.09ALOGPS
pKa (Strongest Acidic)-1.4ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity22.95 m3·mol-1ChemAxon
Polarizability10.43 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0900000000-f83dca3bb4164fb39fc2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-054k-8900000000-111dba10014f3cc5c403View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-9300000000-5cc44eb483ce09d49510View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00e9-6900000000-c1573e4b7aa0acf67018View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0089-9600000000-894c171421adedc823bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-b8c542a1a77eb7a6a191View in MoNA
References
References:
  • Kersten A, Althaus C, Seitz HM, Pfahl HG, Sundmacher R: [Bilateral microsporidial keratitis in an HIV-positive patient with AIDS stage infection] Klin Monatsbl Augenheilkd. 1998 Jun;212(6):476-9. Pubmed: 9715470
Synthesis Reference: Chen, Zhiwen; Liao, Xiangxu; Qian, Weiqiang; et al. Process for preparation of hydroxyalkanesulfonic acids for plating solutions. Faming Zhuanli Shenqing Gongkai Shuomingshu (1990), 6 pp.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID1157
HMDB IDHMDB03903
Pubchem Compound ID7866
Kegg IDC05123
ChemSpider ID7578
WikipediaIsethionic_acid
BioCyc IDCPD-3745
EcoCyc IDCPD-3745

Enzymes

General function:
Involved in alkanesulfonate monooxygenase activity
Specific function:
Involved in desulfonation of aliphatic sulfonates. Catalyzes the conversion of pentanesulfonic acid to sulfite and pentaldehyde and is able to desulfonate a wide range of sulfonated substrates including C-2 to C-10 unsubstituted linear alkanesulfonates, substituted ethanesulfonic acids and sulfonated buffers
Gene Name:
ssuD
Locus Tag:
PA3444
Molecular weight:
41.6 kDa
Reactions
An alkanesufonate (R-CH(2)-SO(3)H) + FMNH(2) + O(2) = an aldehyde (R-CHO) + FMN + sulfite + H(2)O.
General function:
Involved in transporter activity
Specific function:
Part of a binding-protein-dependent transport system for aliphatic sulfonates. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
ssuC
Locus Tag:
PA3443
Molecular weight:
28.5 kDa
General function:
Involved in transporter activity
Specific function:
Part of a binding-protein-dependent transport system for taurine. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
tauC
Locus Tag:
PA3936
Molecular weight:
29.4 kDa
General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex TauABC involved in taurine import. Responsible for energy coupling to the transport system
Gene Name:
tauB
Locus Tag:
PA3937
Molecular weight:
28.8 kDa
Reactions
ATP + H(2)O + taurine(Out) = ADP + phosphate + taurine(In).
General function:
Involved in transporter activity
Specific function:
Part of a binding-protein-dependent transport system for taurine
Gene Name:
tauA
Locus Tag:
PA3938
Molecular weight:
35.9 kDa
General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex SsuABC involved in aliphatic sulfonates import. Responsible for energy coupling to the transport system (Probable)
Gene Name:
ssuB
Locus Tag:
PA3442
Molecular weight:
29.8 kDa

Transporters

General function:
Involved in transporter activity
Specific function:
Part of a binding-protein-dependent transport system for aliphatic sulfonates. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
ssuC
Locus Tag:
PA3443
Molecular weight:
28.5 kDa
General function:
Involved in transporter activity
Specific function:
Part of a binding-protein-dependent transport system for taurine. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
tauC
Locus Tag:
PA3936
Molecular weight:
29.4 kDa
General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex TauABC involved in taurine import. Responsible for energy coupling to the transport system
Gene Name:
tauB
Locus Tag:
PA3937
Molecular weight:
28.8 kDa
Reactions
ATP + H(2)O + taurine(Out) = ADP + phosphate + taurine(In).
General function:
Involved in transporter activity
Specific function:
Part of a binding-protein-dependent transport system for taurine
Gene Name:
tauA
Locus Tag:
PA3938
Molecular weight:
35.9 kDa
General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex SsuABC involved in aliphatic sulfonates import. Responsible for energy coupling to the transport system (Probable)
Gene Name:
ssuB
Locus Tag:
PA3442
Molecular weight:
29.8 kDa